Tag: M.W=200-300

Related Products of 883-44-3,Some common heterocyclic compound, 883-44-3, name is 2-(3-Hydroxypropyl)isoindoline-1,3-dione, molecular formula is C11H11NO3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 30 5-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-2-(oxalyl-amino)thiophene-3-carboxylic acid; To a stirred mixture at 0 C. of 2-(3-hydroxy-propyl)-isoindole-1,3-dione (0.2 g, 0.97 mmol), 0.7 M sodium bromide (0.70 ml, 0.46 mmol), TEMPO (3.0 mg, 0.02 mmol) in dichloromethane (1 ml) was added dropwise a solution of bleach (2.1 ml, 4.9 mmol) and sodium hydrogen carbonate (117 mg, 1.4 mmol). The mixture was stirred at 0 C. for 2 hours after the addition was finished. The mixture was extracted with ethyl acetate (3*20 ml). The combined organic extracts were washed with 10% sodium thiosulphate (3*10 ml), brine (10 ml), dried (MgSO4), filtered and the solvent was evaporated in vacuo. The residue was washed with ethyl acetate (2*1 ml) affording after drying 161 mg (81%) of 3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionaldehyde as a solid. 1H NMR (400 MHz, CDCl3) delta 9.82 (s, 1H), 7.85 (dd, 2H, J=5.6, 2.8 Hz), 7.73 (dd, 2H, J =5.6, 2.8 Hz), 4.04 (t, 2H, J=7.2 Hz), 2.89 (t, 2H, J=7.2 Hz).

The synthetic route of 883-44-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jeppesen, Lone; Andersen, Henrik Sune; Olsen, Ole Hvilsted; Judge, Luke Milburn; Holsworth, Daniel Dale; Bakir, Farid; Axe, Frank Urban; Ge, Yu; US2005/119332; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 20870-78-4, name is 5-Bromoindolin-2-one, A new synthetic method of this compound is introduced below., Quality Control of 5-Bromoindolin-2-one

To a solution of 5-Bromo-1,3-dihydro-indol-2-one (318 mg, 1.5 mmol) and Bis(pinacolato)diboron (420 mg, 1,65 mmol) in dioxane (15 mL) was added KOAc (516 mg, 5.25 mmol). The resulting mixture was degassed, treated with [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium methylene choloride complex (62 mg, 0.075 mmol), heated at 90 C. for 12 h and concentrated. The residue was dissolved in CH2Cl2 (100 mL), washed with water (100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated. The concentrate was purified by flash chromatography on silica gel eluding with 30% ethyl acetate/hexanes to afford 320 mg of Example 133a (82%). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.27 (s, 12H) 3.46 (s, 2H) 6.81 (d, J=7.72 Hz, 1H) 7.49 (m, 2H) 10.51 (s, 1H)) MS (ESI) m/z 260.2 (M+H)+, 276.8 (M+NH4)+

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Iyengar, Rajesh R.; Judd, Andrew S.; Zhao, Gang; Kym, Philip R.; Sham, Hing L.; Gu, Yugui; Liu, Gang; Liu, Mei; Zhao, Hongyu; Clark, Richard F.; Frevert, Ernst U.; Cool, Barbara L.; Zhang, Tianyuan; Keyes, Robert F.; Hansen, Todd M.; Xin, Zhili; US2005/38068; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5332-26-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of LiHMDS (31.3 mL, M in THF) in THF (40 mL) was added at -78C a solution of intermediate A.ii (6.50 g, 26 mmol) in THF (50 mL) over 10 min. After stirring for 1 h at -78C, a solution of N-(bromomethyl)phthalimide in THF (50 mL) was added dropwise over 10 min. The mixture was stirred at -78C for 1 h and then at rt overnight. The resulting solution was quenched with INHCl (260 mL) and extracted with DCM. The combined org. layers were washed with water, dried over MgSO4, concentrated and purified by CC (Hept/EA 1 :1). The resulting solid was triturated with EA to afford the title intermediate as a colourless solid (2.42 g, 23% yield). MS (ESI, m/z): 409.3 [M+H+].

The chemical industry reduces the impact on the environment during synthesis 2-(Bromomethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RITZ, Daniel; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/41194; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 264916-06-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A solution of 2-Boc-5-aminoisoindoline (20mg, 0.085 minol) and a carboxylic acid (0.102 rnmol) in DMF (1 mL) was treated with 1-[bis (dimethylamino)methylene] -1H-1, 2, 3-tr¡Àazolo[4, 5- b]pyridinium 3-oxid hexafluorophosphate (HATU; 39 mg, 0.102 mmol) and i-Pr2NEt (17 pL, 0.102 mmol) . The reaction was allowed to proceed overnight (about 18 hours), after which the solution was diluted with EtOAc (about20 mL) . The diluted reaction was extracted twice with saturated aq. NaHCO3 and once with saturated aq. NaC1. The organic layer was dried over Na2SO4. The products were purified by flash chromatography (SiC2) using an EtOAc/hexanes solvent gradient. Yield: 20.1 mg (78%), white solid, mixtureof rotamers. ?H NMR (600 MHz, ODd3) 7.75 – 7.55 (m,1H), 7.51 (s, 1H), 7.42 – 7.22 (m, 1H), 7.17 and 7.14(d, J = 8.2 Hz, 1H) , 7.05 – 6.92 (m, 1H) , 5.97 and5.95 (d, J = 1.7 Hz, 1H), 4.79 – 4.40 (m, 4H), 1.90(dd, J = 6.9, 1.7 Hz, 3H), 1.51 (s, 9H) . NMR (151MHz, ODd3) 164.2, 154.7, 141.8, 137.7, 125.5,123.2, 123.0, 119.4, 114.5, 79.9, 52.5, 52.2, 52.1,51.8, 28.7, 18.0. HRESI-TOF m/z 303.1702 (C,7H22N203 +H, required 303.1703)

The synthetic route of tert-Butyl 5-aminoisoindoline-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; BOGER, Dale, L.; (104 pag.)WO2017/210206; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Diethyl (aminomethyl)phosphonate was synthesized according to literature procedure (see Kalman et a. Inorg. Chem. 2007, 46, 5260) The compound was isolated as yellow liquid 64% yield (1.082g).?H NMR (300 MHz, CDC13) 4.17-4.08 (m, 4H), 3.01 (d, J 10.3 Hz, 2H), 1.85 (bs, 2H), 1.34 (t, J 7.1 Hz, 6H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(Bromomethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY; TSANTRIZOS, Youla S.; POIRIER, Judes; SEBAG, Michael; BERGHUIS, Albert; PARK, Jaeok; WIM DE SCHUTTER, Joris; WO2014/78957; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, molecular formula is C16H13NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Product Details of 101207-45-8

Add 50 mg of 2- (4-methylbenzyl) -isoindololine-1,3-dione (0.2 mmol), 1.2 mg of potassium hydroxide to a glass test tube with magnetons,Add 2 ml of isopropanol under nitrogen protection,Adding 20 microliters of 0.001M catalyst (S / C = 10,000),Subsequently, the reaction flask was transferred to an autoclave, the reaction kettle was tightened, 3 MPa of hydrogen was charged, and the reaction was carried out at 40 C for 20 hours. After the reaction was completed, the mixture was naturally cooled to room temperature, and the hydrogen gas was carefully released. The celite was filtered, and the organic solvent was removed from the filtrate to obtain 51 mg of a white solid with a yield of 99%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 101207-45-8, its application will become more common.

Reference:
Patent; South University of Science and Technology of China; Ma Baode; Shao Panlin; Wu Chao; Wang Jiang; Zhang Xumu; (12 pag.)CN110734384; (2020); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 18711-13-2,Some common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, molecular formula is C8H3Cl2NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a solution of isatin 1 (1 mmol) in toluene (5 mL) was added the solution of trialkyl/aryl Al 2 (2 mmol, 2 M in toluene) dropwise at RT. Then the mixture was heated at 70 C and stirred for additional 3-3.5 h (see Table 2). The reaction was monitored by TLC. After completion of the reaction, toluene was evaporated and extracted with ethyl acetate (3 ¡Á 5 mL). The combined organic layer was washed with brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography using ethyl acetate/hexanes (4:1-1:1). All compounds were characterized by (MP, NMR, Mass, and IR) spectral data.18

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4,7-Dichloroindoline-2,3-dione, its application will become more common.

Reference:
Article; Kumar, G. Santosh; Ramesh, Palakuri; Kumar, A. Sanjeeva; Swetha; Meshram; Tetrahedron Letters; vol. 54; 37; (2013); p. 5048 – 5051;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 169037-23-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 169037-23-4 name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a solution of isatin (0.2 mmol) and indole (0.2 mmol) in pyridine (0.5 mL) was added K2CO3 (0.2 mmol) under an airatmosphere and the mixture was stirred at 40C for 2 h. Then,morpholine (0.3 mmol), CuI (0.04 mmol), and benzoic acid(0.1 mmol) were added to the reaction mixture and the resultingmixture was heated at 80C for another 5 h. The reaction mixturewas concentrated under reduced pressure. The residue was puriedby ash chromatography on silica gel (eluent: EtOAc/PE 1:1) toyield the corresponding product 4a.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-(Trifluoromethoxy)indoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Peng, Xiangjun; Xu, Xianyun; Chen, Shuangyang; Tian, Zeng; Liu, Liangxian; Liu, Qian; Tetrahedron; vol. 74; 13; (2018); p. 1505 – 1512;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 129487-92-9 as follows. name: tert-Butyl 5-aminoindoline-1-carboxylate

The 1-tert-butoxy-carbonyl-5-amino indoline (3g, 14mmol) dissolved in water (3 ml) in, cooling to-5-0 C degrees, dropping sodium nitrite (1.16g, 16 . 8mmol) of water (3 ml) solution, 0 C stirring for 30 minutes, a diazo reaction liquid obtained, the spare; sodium acetate (2.64g, 32 . 2mmol) dissolved in water (3 ml) in, by adding 2-chloro acetyl ethyl acetate (2.3g, 14 . 0mmol) second grade fat of the acetic acid (5 ml) solution, cooled to 0 C, spare the dropping of a diazo reaction solution, 0 C reaction 1 hour. Adding water to the reaction solution (50 ml), ethyl acetate (50 ml ¡Á 3) extraction, combined organic phase, the organic phase with water (50 ml ¡Á 2) washing, dry anhydrous sodium sulfate, concentrated, the title compound ethyl 2-chloro-2-(2-(indolin-5-yl)hydrazono)acetate (25B), yellow solid (1.2g, yield 32%).

According to the analysis of related databases, 129487-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO LTD; WEI, YONGGANG; QIU, GUANPENG; LEI, BAILIN; LU, YONGHUA; (120 pag.)CN104395312; (2016); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, molecular formula is C10H9Cl2NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. SDS of cas: 118289-55-7

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 118289-55-7, its application will become more common.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem